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Chicago’s Mayoral Candidates, Ranked by Chances of Victory

E very week during the baseball season, ESPN publishes its power rankings of all 30 teams in the MLB. In Chicago, more than half that many people are running for mayor, so we thought we’d do the same for them.

As of the November 26 filing deadline, 21 candidates had turned in petitions to run for mayor of Chicago — the largest field since at least 1901, according to the Chicago Board of Elections. Our latest Mayoral Power Rankings covers most of them.

(Sandra Mallory, Roger Washington, Richard Mayers, Catherine Brown D’Tycoon, and Conrien Hykes Clark also filed petitions, but according to the Tribune, they hadn’t assembled campaign committees, launched a campaign website, or raised any money — reliable indicators that they won’t make the ballot.)

Cook County Board President Toni Preckwinkle is still the favorite, but she has a new top challenger: Illinois Comptroller Susana Mendoza.

1 TONI PRECKWINKLE

The latest mayoral poll, conducted by Global Strategy Group, has Preckwinkle in the lead, with 15 percent compared to Susana Mendoza’s 13 percent. But it also found that Preckwinkle has higher negative ratings than Mendoza (31 percent to 14 percent). Those weaknesses foreshadow “a negative campaign for her versus Mendoza,” the pollsters predict.

Preckwinkle isn’t waiting for a runoff to bash her chief opponent. At “The Great Displacement,” a November 18 mayoral forum on black issues at the CTU headquarters, Preckwinkle attacked Mendoza for her past support of the death penalty.

“[She] even said at one point she would be happy to flip the switch,” Preckwinkle said.

Mendoza countered that her past support for the death penalty was a response to crime in Little Village, which her family fled for the suburbs when she was 7. As a state legislator, she voted to abolish capital punishment.

Preckwinkle’s Twitter feed also called Mendoza “an ally of Rahm, Madigan, and Ed Burke. A vote for Mendoza,” she continued, “is a vote for the machine that got us into our current mess.”

Beneath Preckwinkle’s sensible spectacles is a canny, unsentimental politician. As chair of the Cook County Democratic Party, Preckwinkle has her own Machine, and she’ll attempt to run Mendoza over with it. (According to NBC Chicago, Preckwinkle has 200 workers examining her opponents’ petitions, including Mendoza’s. In the words of Chicago’s own David Mamet, “Old age and treachery will always beat youth and exuberance.”

Preckwinkle recently burnished her progressive credentials by participating in a protest at the Chatham Target store, calling its imminent closure a “public disinvestment in the African-American community.”

2 SUSANA MENDOZA

Don’t hold it against Mendoza that she ran for re-election as Illinois comptroller when she was really planning to run for mayor. Nobody wants to be comptroller, the official with the unglamorous task of signing the state’s checks. It’s a stepping stone office. Almost everyone who held it before Mendoza ran for either governor or senator. (They all lost, so it’s also been a dead-end office.)

The Global Strategy Group poll contained a lot of good news for Mendoza. “After hearing positive information about Mendoza, Preckwinkle, [Bill] Daley, and Gery Chico, nearly a quarter of voters choose Mendoza on their full ballot (23%), an increase of 10 points, to overtake Preckwinkle for the lead,” the pollsters found.

They also found that “[i]n the event that Mendoza and Preckwinkle continue as voters’ top-two choices, nearly four in 10 voters would choose Mendoza over Preckwinkle in the April run-off (Mendoza 39%/Preckwinkle 33%).”

If that happens, it will be a historic run-off: between two women from minority communities who also happen to be the most prominent officeholders in the field.

It will also be a nasty one, as Mendoza and Preckwinkle aren’t even waiting until they have the ballot to bite into each other. Mendoza has needled Preckwinkle for her support of an unpopular and later repealed sweetened beverage tax, and for her alliance with outgoing Cook County Assessor Joe Berrios.

Also problematic: Mendoza is getting flak from progressive Latinos. Ald. Rick Munoz, an ally of Rep.-elect Chuy Garcia, called Mendoza out for “starting under the corrupt Hispanic Democratic Organization, which basically was disbanded after several of its leaders got indicted for patronage efforts.”

Mendoza won her first election the state legislature with the help of Southwest Side boss of bosses Ed Burke, whose office was recently raided by the FBI. On the other hand, Ed Burke and the HDO have won a lot of elections.

3 PAUL VALLAS

If this campaign were about who has the most well thought out platform, Vallas would win easily. When Chicago has a problem, Vallas has a plan. Lead service lines to city homes? Replace them by establishing a Neighborhood Conservation Fund to gather federal, state, and local dollars. Woebegone neighborhood business districts? Rebuild them with $1 billion in TIF funds dedicated to so-called “Opportunity Zones.” Schools with declining enrollment? Rather than close them like Rahm Emanuel did, turn them into specialized educational institutions.

“A declining school on the West Side could be converted into an already needed agricultural science school,“ the former CPS CEO said in a November 15 speech. “A struggling high school could be re-invented as a first responders academy. Closed schools or schools on the verge of closing could be re-purposed as adult high schools via funding available under a state law, or [as] alternative schools.”

On Vallas’s website, he calls himself “A Problem Solver, Not a Politician.” He has never held political office, instead serving in a series of bureaucratic positions: budget director and revenue director in Chicago, schools superintendent in Philadelphia and New Orleans. He’s a big thinker. But does he have the chops to win an election and run a city?

4 AMARA ENYIA

Enyia added a dose of celebrity to the race when Chance the Rapper endorsed her in October, vaulting the little-known 35-year-old director of the Austin Chamber of Commerce into the citywide consciousness. Chance’s father, Ken Bennett, is Preckwinkle’s campaign chairman, so the rapper’s choice of Enyia represents a generational change in Chicago politics, away from older progressives seeking to recapture the magic of Harold Washington.

Chance didn’t just endorse Enyia — he is actively campaigning with her. They appeared together at events in Pritzker Park and Woodlawn, and he hosted a fundraiser for her at Chicago Chop House. Chance’s involvement also inspired Kanye West to donate $200,000 to Enyia, enough to pay off campaign finance violation fines dating back to her aborted 2015 mayoral run.

Enyia is promoting one of the campaign’s more original ideas: a public bank that she says would “generate hundreds of millions of dollars in revenue for the city, eliminate hundreds of millions of dollars in interest rate costs and fees currently paid to private banks, reduce corruption, and guarantee more responsible use of funds to promote economic growth.” Ald. Ameya Pawar, who is running for city treasurer, also favors creating a public bank.

While Enyia seems unlikely to win, she could follow the same path as state Sen. Patricia Van Pelt, a 2011 mayoral candidate who parlayed a losing run into a less prestigious office.

5 GERY CHICO

A serious, thoughtful guy, Chico knows all the important people in Chicago, and he’s raised a lot of money from them.

In his first digital ad, he talks about taking over as board president of Chicago Public Schools — from which he, his parents, and children all graduated — in 1995, when the legislature transferred control from an elected school board to the mayor. Chico takes credit for building 65 new facilities and improving student performance for the six years he led the board. What he doesn’t mention is that Vallas was CEO during that entire period.

Despite his competence, connections, and city bona fides, it’s hard to see where Chico finds a constituency in this race. He overlaps too much with Vallas, who has a stronger record as a school reformer, and Mendoza, another Southwest Side Latinx groomed by Ed Burke. (Burke is supporting Chico, who got his start in city politics as an aide to Burke’s Finance Committee.)

6 BILL DALEY

Daley is the Jeb Bush of this campaign: a younger son trying to prolong a political dynasty past its expiration date. He has raised more money than anyone else — $2.4 million from such big donors as Cindy Pritzker and Pat Ryan — but he must be campaigning in board rooms and Streeterville condos, because he hasn’t been visible on the campaign trail.

Daley made a bit of news for proposing a $50 million Office of Violence Prevention and Reduction, run by a deputy mayor, to curb gun crime. His website promises a series of Neighborhood Conversations, but doesn’t list any on the schedule.

A Daley ran Chicago for 43 of the 56 years between 1955 and 2011. That’s enough for one family. Bill missed his chance to be mayor in 1942, when his big brother Rich was born six years before he was.

7 GARRY McCARTHY

Rage Against the Machine is not likely Garry McCarthy’s favorite band, but it seems to be the theme of his campaign. Currently, a tweet reading “Our Movement Will Beat the Machine” is pinned at the top of his profile. He’s also blamed the city’s failure to tame its gangs and lower the murder rate, as his native New York City did, on its hyperpoliticized culture.

“It’s not going to change unless someone changes it,” McCarthy says. “You’ve got to hit it with a hammer.”

McCarthy’s complaints about machine politics, though, mark him as an outsider who doesn’t understand Chicago. (So does his stance against dibs, which he says “causes conflict.”) Machine politicians win most of the elections here. You get ahead in politics by either working your way up through the Machine, as Mendoza did, or taking over the Machine, as Preckwinkle did. They’re the front runners because they’ve played the game better than anyone else in the field.

In our first power rankings, we put McCarthy at No. 2, because it appeared that his silent minority of law-and-order voters on the Northwest and Southwest sides was large enough to help him squeak into the runoff. Since then, though, Mendoza has entered the race, and she seems capable of building a larger coalition than McCarthy.

McCarthy was pointedly not invited to “The Great Displacement,” the aforementioned forum on black issues at CTU headquarters. Wrote the organizers, United Working Families: “We refuse to give air time to the man who covered up the police murder of LaQuan [sic] McDonald. From covering up the murder of an innocent Black teenager to doctoring crime statistics to accepting campaign contributions from Trump supporters, McCarthy has repeatedly demonstrated his callous disregard for Black and Latinx people. Garry McCarthy is a national disgrace. He is unwelcome at our forum, and unwelcome in Chicago.”

The progressive electorate of 2019 just may not be in the mood for a white guy, which is not just a problem for McCarthy, but for Vallas, Chico, Daley, Joyce, and Kozlar, too.

8 LORI LIGHTFOOT

The former chair of the Chicago Police Board and the Police Accountability Task Force, convened to fix the department after the Laquan McDonald shooting, Lightfoot staked out a position as a candidate who would end police misconduct. She has also criticized the $95 million police academy soon to be built in Austin, saying it was planned without community input.

Lately, Lightfoot has been talking more about housing. She’s suggested a citywide approval process for affordable housing projects, so they can’t be blocked with aldermanic privilege, and a progressive real estate transfer tax, starting at 0.35 percent for properties under $500,000, and rising to 3 percent for properties of over $5 million.

Those are the proper progressive positions, but with higher-profile far-left candidates in the race, Lightfoot isn’t getting much attention.

9 DOROTHY BROWN

According to the Sun-Times’s Mayoral Money Tracker, Brown’s largest donation has been $20,000 from the Chi-Lites, who headlined a November 1 fundraiser for her.

That’s no match for the $100,000 Toni Preckwinkle received from the Service Employees International Union Local 1, or the $50,000 Bill Daley got from Paul Meister, vice chairman of Grosvenor Capital.

University of Illinois-Chicago political science professor Dick Simpson estimates it will take $5 million to win the race, and if that’s true, Brown is in trouble. She can also expect a petition challenge, along with Enyia and Mendoza, after turning in sheets on which the handwriting for every voter was identical.

10 WILLIE WILSON

No one has contributed more generously to Willie Wilson’s campaign than… Willie Wilson. The businessman, who made millions running McDonald’s restaurants and importing medical supplies, has gifted himself more than $700,000, enough to put his face on billboards all over the city.

According to the Sun-Times, “$19,000 of the $771,000 his campaign has banked has come from anyone other than Wilson himself.” Wilson’s self-funding was enough to erase state-imposed limits on campaign donations across the board, allowing any candidate to accept any amount of money from anyone.

Wilson placed third in the 2015 mayor’s race with 10 percent of the vote, in a field where he was the only serious black candidate. Then he ran for the Democratic nomination for president, competing in eight primaries but never earning more than one-half of one percent of the vote. This race is Wilson’s latest self-funded ego trip.

11 JA’MAL GREEN

Green seemed miffed that his old friend Chance the Rapper, who he’s known since their days in a youth program together, chose instead to endorse Amara Enyia. Green scheduled a City Hall press conference immediately following Chance and Enyia’s, then didn’t show up for it. Later, he told the Sun-Times he found it “insulting” that Chance hadn’t called to give him the news ahead of time.

As much as any other candidate, Green is a presence in the city’s most neglected neighborhoods. His campaign headquarters is on 87th Street in Auburn-Gresham. On Thanksgiving, he gave away meals — and held a voter registration drive — in Altgeld Gardens, the deep South Side housing project that recently lost its only grocery store.

12 JERRY JOYCE

The classic Chicago accent is disappearing from our city’s politics. Only a handful of aldermen still speak with one: Nick Sposato and Anthony Napolitano, both ex-firefighters from the Far Northwest Side, and Patrick Thompson, a grandson of Mayor Richard J. Daley.

If you’re looking for a mayor who knows how to express himself in Chicagoese, listen no further than Joyce. He’s not a “dese, dem, and dose” guy, but he’s got the hard consonants and elongated vowels. “I’ve cared about Chicawgo my whole life,” he says in his campaign video. “Coaching, mentering, being invahlved in the neighborhood, have all contributed to my love of our city.” It should help him in his native Beverly, one of the last strongholds of the old-school accent.

13 LA SHAWN K. FORD

The West Side state representative wants to bring the glamour and prosperity of downtown to his neighborhood. “Chicago is a beautiful city. What we have going on downtown, we want to spread that throughout the city, so that all of Chicago is beautiful,” he told Fox32’s Good Day Chicago.

To do that, Ford wants to build a technology and manufacturing trade school. Job training, he says, will reduce violence. However, the Sun-Times doesn’t list a single donation to Ford’s campaign.

14 BOB FIORETTI

Meet a man in search of an office ever since his 2nd Ward was moved from the Near South Side to the Near North Side, thus drawing him out of a City Council seat. Fioretti ran for mayor in 2015, challenged Preckwinkle for Cook County Board president in this year’s primary, and is now making a second run for mayor. He didn’t decide to enter the race until the last day of petition filing, giving him a late start on the rest of the field.

15 NEAL SALES-GRIFFIN

Filed petitions with only 18,000 signatures, far below the 37,500 considered necessary to survive a challenge. He may not be in the race long enough for voters to learn his name is pronounced “SAH-lez GRIFF-in.” A 30-year-old web developer who does podcasts, he’s hipper than any of the political hacks he’s running against.

16 JOHN KOZLAR

Kozlar, a 29-year-old Bridgeport native, has lost two races for 11th Ward alderman. Now, he’s decided to take the next step and lose a citywide race. His most original proposal: shifting city employees who start work in 2020 and after from defined benefit pensions to 401Ks.